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Frustrated with CIA, Trump administration turned to Pentagon for shadow war with Iran

·National Security Correspondent
·11 min read
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In the final month of his presidency, Donald Trump signed off on key parts of an extensive secret Pentagon campaign to conduct sabotage, propaganda and other psychological and information operations in Iran, according to former senior officials who served in his administration.

The campaign, which was to be led by the military’s Special Operations forces, was designed to undermine the Iranian people’s faith in their government as well as shake the regime’s sense of competence and stability, according to those former officials.

The plan, which eventually grew to a 200-page package of options, involved “things that would cause the Iranians to doubt their control over the country, or doubt their ability to fight a war,” said a former senior defense official.

Then-President Donald Trump speaks to the press during a news conference in the James Brady Press Briefing Room of the White House on Sept. 16, 2020.
Then-President Donald Trump at the White House in September 2020. (Alex Wong/Getty Images)

While being briefed on elements of the campaign, Trump acknowledged that it would have to be carried out by the incoming Biden administration, according to the former official.

It is unclear whether the Biden administration has continued to pursue the Trump-approved operations. But with the White House set to resume indirect nuclear talks with Iran in Vienna later this month, U.S. officials may have to decide whether the Trump-approved Pentagon campaign could jeopardize negotiations — or help compel Iran to an agreement.

It’s representative of a dilemma that was also faced by President Biden’s predecessors: how hard to prosecute the shadow war against Iran while also seeking to negotiate with Tehran.

The Department of Defense and the CIA declined to comment. The White House referred queries to the Pentagon.

Though the plan did not include targeted killings, the likelihood that Iranians might die during “kinetic” acts of sabotage and other operations — and because Iran itself was not considered a war zone — meant the Pentagon needed to receive approval from the president to move forward, according to former officials.

In fact, said former officials, many prongs of this “irregular warfare” campaign did not formally require presidential permission, and could have been approved by the secretary of defense and other top Pentagon officials.

But some in the Pentagon, especially within the Joint Staff, impeded the execution of these plans for years, according to former officials.

By early 2018, “very explicit direction went out” to the Pentagon on some elements of the campaign, said a former senior administration official. “Explicit direction was given; it was understood. And discretion was exercised liberally not to do it.”

Gen. Mark Milley, chairman of the Joint Chiefs of Staff, escorts incoming Defense Secretary Lloyd Austin III to the Pentagon on Austin's first day in his new role on Jan. 22, 2021, in Arlington, Va.
Gen. Mark Milley, chairman of the Joint Chiefs of Staff, escorts incoming Defense Secretary Lloyd Austin III to the Pentagon on Austin's first day in his new role on Jan. 22, 2021. (Sarah Silbiger/Getty Images)

“The Pentagon sat on it, refusing to take any action on it, because it didn’t want to,” said the former official. “And ultimately, at a point of exasperation, felt it had no choice or recourse but to present some of the components of it, as some broad plan to be approved in response to a task, so they wouldn’t look like they were completely resistant or incompetent.”

The last-minute push was the culmination of years of frustration by Trump administration officials over how to wage the shadow conflict with Iran. “The Joint Staff and CIA were obstructing everything,” said the former senior defense official.

The ex-official stressed that the plan, which aimed to weaken the Iranian government, was designed to deter a war, and not precipitate an overt military conflict with Tehran.

“It’s a very detailed escalation ladder,” said the former official. “It’s not like all of a sudden you go from zero to 60.”

Some of these actions would not be executed until the U.S. and Iran were “just at the brink” of war, said the source.

The proposed campaign was intensely scrutinized by Pentagon legal personnel, according to Trump-era officials. One of the “sticking points” within the Department of Defense was “the legality of it, whether this [campaign] constituted acts of war,” said a former senior Pentagon official. “It all came down to the definition of sabotage, and what that means legally.” Pentagon lawyers were also focused on actions that might increase “the likelihood of provoking war,” said the former senior defense official.

The proposal was developed and supported by top uniformed officials within the military’s Special Operations Command and Central Command, as well as senior civilians within the Defense Department overseeing special operations and intelligence matters, according to former officials.

Gen. Frank McKenzie, the head of U.S. Central Command, was an ardent proponent of the Iran-focused actions, according to former officials, who said Gen. Mark Milley, chairman of the Joint Chiefs of Staff, consistently slow-rolled the proposal.

Gen. Mark A. Milley, chairman of the Joint Chiefs of Staff, testifies during a House Armed Services Committee hearing on ending the U.S. military mission in Afghanistan in the Rayburn House Office Building at the U.S. Capitol on Sept. 29.
Gen. Mark Milley, chairman of the Joint Chiefs of Staff, testifies during a House Armed Services Committee hearing in September. (Rod Lamkey-Pool/Getty Images)

The heads of Central Command and Special Operations Command “were furious at the Joint Staff,” said the former senior defense official. “Because they felt that Milley sitting on the package ... was actually tying their hands and putting American forces at risk. Because they weren’t able to build up the capabilities to deter Iran before a conflict.”

“The allegations here simply aren’t true,” said a spokesman for Milley. “Without commenting on any action for security reasons, Gen. Milley’s job as the chairman is to give military advice to our civilian decision makers. He gives advice by articulating the assessed risk and benefits of military action. He did this in the Trump administration, and he does this now.”

The plan, which officials said had been under development for years, involved operations that would take at least six months to get up and running once they were approved by the president. “Trump was briefed that none of these things were going to take place in his time” in office, said the former senior defense official.

President Trump reacted more with “supreme disappointment” that these options were only now being presented to him, said the former senior administration official.

Former officials described an interagency process on Iran that was rife with dysfunction. The CIA and Defense Department “were not providing good options to the decision makers, to the president,” because they thought Trump was “crazy and if they took [an] idea to him he’d say, ‘Do it,’ and so they felt they had to control him,” said former acting Secretary of Defense Chris Miller, who also served in a number of NSC and Pentagon positions in the Trump administration.

Within the Pentagon, some top officials tried to steer the administration away from an overt attack on Iran by pushing for sub rosa, deniable options, which they believed would give the Iranians more room to save face and not precipitate a military response from Tehran.

Defense Secretary Jim Mattis speaks at a reception as President Donald Trump looks on at the White House in 2018.
Defense Secretary Jim Mattis speaks at a White House reception in 2018 as then-President Donald Trump looks on. (Nicholas Kamm/AFP via Getty Images)

“[Defense] Secretary [Jim] Mattis’s general order No. 1 to me was, ‘We don’t want a war with Iran,’” said Mick Mulroy, the former deputy assistant secretary of defense for the Middle East. “One of the things that I proposed to take the steam out of the White House … was to do things like irregular-warfare-type stuff.”

The CIA, with its focus on covert action, was a natural ally, according to Mulroy.

The CIA’s Iran chief understood the White House-Pentagon dynamic — and the Pentagon’s desire to avoid overt conflict — and proposed initiating “internal-strife-type things” and propaganda-oriented covert operations against Iran at National Security Council meetings, said a second former senior Pentagon official.

But it’s not clear how many, if any, of the agency’s proposals actually came to fruition.

The CIA’s Iran Mission Center was doing “nothing” on Iran, said the former senior administration official. “And I’m being very, very charitable when I say nothing.”

Frustration with the agency was intense. “We would get briefed on all these wild, elaborate plans for various operations that never occurred,” said Victoria Coates, who served as deputy national security adviser for Middle East and North African Affairs.

Skepticism pervaded the relationship between top Trump national security officials and their CIA briefers. Administration officials pointedly questioned the agency’s assessments that Iran was not imminently capable of developing nuclear weapons, according to former officials.

In the end, Trump national security officials concluded that, though the CIA may have been obstructing their directives on Iran, the agency likely did not possess the capabilities to carry out the types of covert action demanded by administration policymakers.

When it came to covert action against Iran, administration officials asked the CIA, “What can we do tonight? Or what can we do next week? Or even six months from now?” said the former senior Pentagon official. “It was the ‘come to Jesus’ moment, [and] it’s like, 'That’s it, that’s all you’ve got?'” The agency’s capabilities were “completely underwhelming,” said this former official.

Then-CIA Director Gina Haspel arrives on Capitol Hill on Jan. 8, 2020, for a closed briefing on the operation that led to the death of Iranian Gen. Qassem Soleimani.
Then-CIA Director Gina Haspel on Capitol Hill in 2020. (Brendan Smialowski/AFP via Getty Images)

The CIA engaged in “this constant litany of why we couldn’t do anything, and then you have the Israelis champing at the bit to do stuff, and wondering why we would talk a good game and then go back and not produce anything,” said Coates.

Eventually, Trump told the Israelis, “'Go forth. Go, do. You be the kinetic arm, and we’ll do the maximum pressure campaign,'” said a second former senior administration official.

Meanwhile, then-CIA Director Gina Haspel was working to convince Milley that the agency should be in charge of the U.S.’s secret operations against Iran, according to the former senior defense official.

Haspel “wooed him into believing that CIA was responsible for this, and let CIA take care of this,” said this former official. “Meanwhile, CIA wasn’t doing anything.”

CIA and other officials strongly dispute this characterization. Long-running CIA programs and authorities — focused on countering Iran’s nuclear program, sowing dissent within the regime and delegitimizing it in the eyes of the Iranian public, and combating Iranian influence abroad, among other things — continued under the Trump administration, according to former agency and national security officials.

On counterproliferation-related activities, “they let us run wild, because they just didn’t want to get involved in the disruption part,” said the former senior agency official. In fact, argue some former CIA officials, during the Trump administration, the agency’s Iran center was so focused on covert action that it hurt the agency’s ability to develop Iranian source networks.

In 2018, the Trump administration also approved a new presidential finding permitting the CIA to conduct much more aggressive covert action in cyberspace. The agency subsequently conducted covert hack-and-dump operations against Iran and Russia and cyberattacks on Iranian infrastructure, former officials told Yahoo News. The secret authorization also freed up the agency to conduct these operations with less White House oversight.

A man crosses the Central Intelligence Agency seal in the lobby of CIA headquarters in Langley, Va.
The agency seal in the lobby of CIA headquarters in Langley, Va. (Saul Loeb/AFP via Getty Images)

But the issues went deeper than neglect, benign or not, by the Trump administration, according to another former CIA official. When it came to the administration’s ideas for covert action against Iran, “either it was overly aggressive — start a war or people die — or unrealistic,” said this former official. “Human life was not so much a concern.”

The agency’s diminished covert action capabilities in Iran may have been tied to its struggles in maintaining sources there, according to former officials. “The stable has been decimated, and there was no incentivization to rebuild it,” said the former senior CIA official.

Indeed, in the summer of 2021, the top CIA official abroad responsible for Iran operations sent a cable to agency headquarters warning that its Iran-related recruiting efforts had all been compromised, according to former CIA officials. The Iran-related cable was previously reported by the New York Times.

In October, the CIA dissolved its Iran Mission Center, folding it back into the agency’s broader Middle East operations division. Some former officials hope the agency will now refocus on more traditional intelligence-gathering activities.

“We need to understand what’s going on there, what’s happening,” said a second former senior CIA official. The lack of sourcing “has reverberated into what amounts to an operational disaster on the Iranian target.”

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